TWI555528B - 泛醇基二十二碳六烯酸酯及其於治療與預防心血管疾病的用途 - Google Patents

泛醇基二十二碳六烯酸酯及其於治療與預防心血管疾病的用途 Download PDF

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Publication number: TWI555528B
Authority: TW; Taiwan
Prior art keywords: acid; panthenol; docosahexaenoate; formula; dha
Prior art date: 2010-08-11

Application number

TW100127261A

Other languages

English (en)

Chinese (zh)

Other versions

TW201208672A (en

Inventor

費德奎連通尼

羅伯特雷廷尼

帕莎拉吉伊利莎白都彭

Original Assignee

皮爾法伯製藥公司

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2010-08-11

Filing date

2011-08-01

Publication date

2016-11-01

2011-08-01 Application filed by 皮爾法伯製藥公司 filed Critical 皮爾法伯製藥公司

2012-03-01 Publication of TW201208672A publication Critical patent/TW201208672A/zh

2016-11-01 Application granted granted Critical

2016-11-01 Publication of TWI555528B publication Critical patent/TWI555528B/zh

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208000024172 Cardiovascular disease Diseases 0.000 title description 8
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MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 53
229940101267 panthenol Drugs 0.000 claims description 20
235000020957 pantothenol Nutrition 0.000 claims description 20
239000011619 pantothenol Substances 0.000 claims description 20
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235000020669 docosahexaenoic acid Nutrition 0.000 claims description 19
238000000034 method Methods 0.000 claims description 9
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
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Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Hospice & Palliative Care (AREA)
Obesity (AREA)
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Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

TW100127261A 2010-08-11 2011-08-01 泛醇基二十二碳六烯酸酯及其於治療與預防心血管疾病的用途 TWI555528B (zh)

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FR1056560A FR2963790B1 (fr)	2010-08-11	2010-08-11	Docosahexaeneoate de panthenyle et son utilisation dans le traitement et la prevention des maladies cardiovasculaires

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US (2)	US20130137768A1 (fr)
EP (1)	EP2603486B1 (fr)
JP (1)	JP5960695B2 (fr)
KR (1)	KR20140031830A (fr)
CN (1)	CN103025707B (fr)
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AU (1)	AU2011288410B2 (fr)
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CA (1)	CA2806154A1 (fr)
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DK (1)	DK2603486T3 (fr)
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FR (1)	FR2963790B1 (fr)
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IL (1)	IL224632A (fr)
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PL (1)	PL2603486T3 (fr)
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SI (1)	SI2603486T1 (fr)
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DE102011014386A1 (de) *	2011-03-11	2012-09-13	Hemoteq Ag	Endoprothese mit einer Wirkstoffbeschichtung
FR2998479B1 (fr) *	2012-11-27	2017-04-28	Pf Medicament	Utilisation d'un ester de dha pour le traitement prophylactique et/ou curatif de la drepanocytose
PL3176164T3 (pl)	2014-07-30	2020-05-18	Aetas Pharma Co. Ltd.	Izomer optyczny pochodnej 1-tlenku 1,4-benzotiazepiny oraz farmaceutyczna kompozycja wytworzona z jego użyciem

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW200811108A (en) *	2006-06-23	2008-03-01	Pf Medicament	DHA esters and use thereof in treatment and prevention of cardiovascular disease

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ITMI20022511A1 (it)	2002-11-26	2004-05-27	Victorix Assets Ltd	Uso di composizioni farmaceutiche contenenti esteri etilici di acidi poliinsaturi omega-3 nella orevenzione della fibrillazione atriale.
FR2949063B1 (fr) *	2009-08-11	2011-09-30	Pf Medicament	Composition pharmaceutique comprenant un ester de dha destinee a etre administree par voie parenterale

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW200811108A (en) *	2006-06-23	2008-03-01	Pf Medicament	DHA esters and use thereof in treatment and prevention of cardiovascular disease

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RU2593203C2 (ru)	2016-08-10
AU2011288410A1 (en)	2013-03-21
AU2011288410B2 (en)	2014-05-22
ES2531437T3 (es)	2015-03-16
HK1180298A1 (en)	2013-10-18
JP5960695B2 (ja)	2016-08-02
US20130137768A1 (en)	2013-05-30
EP2603486A1 (fr)	2013-06-19
EP2603486B1 (fr)	2014-12-17
DK2603486T3 (en)	2015-03-02
MY166065A (en)	2018-05-23
RU2013110131A (ru)	2014-09-20
CN103025707A (zh)	2013-04-03
UA109551C2 (uk)	2015-09-10
HUE024560T2 (hu)	2016-02-29
FR2963790A1 (fr)	2012-02-17
AR082594A1 (es)	2012-12-19
CN103025707B (zh)	2015-04-29
MX2013001506A (es)	2013-02-27
JP2013538197A (ja)	2013-10-10
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